benzyl 5-chloro-2-oxo-2,3-dihydro-indole-1-carboxylate | 197776-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: benzyl 5-chloro-2-oxo-2,3-dihydro-indole-1-carboxylate
• 英文别名: benzyl 5-chloro-2-oxoindoline-1-carboxylate；benzyl 5-chloro-2-oxo-3H-indole-1-carboxylate
• CAS: 197776-04-8
• 化学式: C₁₆H₁₂ClNO₃
• 分子量: 301.729
• InChiKey: QRNBKTLYJRLGBR-UHFFFAOYSA-N

物化性质

• 沸点：
  457.5±55.0 °C(Predicted)
• 密度：
  1.394±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 5-chloro-2-oxo-2,3-dihydro-indole-1-carboxylate 在 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  Synthesis of 1,3-Di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles

  摘要：

  Two protocols have been developed for the synthesis of 1,3-di[alkoxy(aryloxy)carbonyl]-2-oxo-2,3-dihydroindoles starting from the corresponding N,O-diacyl derivatives obtained by treatment of 2-oxindoles with chloroformic acid esters and, triethylamine. The first is rearrangement of N,O-diacylated compounds in the presence of 4-dimethylaminopyridine to give N,C(3)-diacylated products with identical acyl groups in the two positions. The second involves O-deacylation of the N,O-diacylated compounds, followed by O-acylation and rearrangement resulting N,C(3)-diacylated 2-oxindoles with different acyl groups in the two positions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00477-4
• 作为产物：
  描述：

  benzyl 2-{[(benzyloxy)carbonyl]oxy}-5-chloro-1H-indole-1-carboxylate 在 碳酸氢铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl 5-chloro-2-oxo-2,3-dihydro-indole-1-carboxylate
  参考文献：
  名称：

  羟吲哚衍生物的新途径

  摘要：

  拟定了一种新的，实用的抗风湿性吲哚衍生物替尼达普的合成方法。该新方法已经开始了对羟吲哚酰化反应机理的研究。已经开发了用于从氧吲哚开始合成1- [烷氧基（或芳氧基）羰基]-和1，3-二[烷氧基（或芳氧基羰基）羰基]氧吲哚的方法。为tenidap设计的路线也提供了对几种类似物的便捷访问。

  DOI：

  10.1007/s00706-003-0127-9

文献信息

• Tricyclic spiro derivatives as CRTH2 modulators
  申请人：Schwarz Matthias

  公开号：US20090318486A1

  公开（公告）日：2009-12-24

  The present invention is related to the use of spiro derivatives of Formula (I) for the treatment and/or prevention of allergic diseases, inflammatory dermatoses and other diseases with an inflammatory component. Specifically, the present invention is related to the use of spiro derivatives for the modulation of CRTH2 activity.

  本发明涉及使用式(I)的螺环衍生物用于治疗和/或预防过敏性疾病、炎症性皮肤病和其他具有炎症成分的疾病。具体而言，本发明涉及使用螺环衍生物来调节CRTH2活性。
• WO2006/125784
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery of a New Class of Potent, Selective, and Orally Bioavailable CRTH2 (DP2) Receptor Antagonists for the Treatment of Allergic Inflammatory Diseases
  作者：Stefano Crosignani、Patrick Page、Marc Missotten、Véronique Colovray、Christophe Cleva、Jean-François Arrighi、John Atherall、Jackie Macritchie、Thierry Martin、Yves Humbert、Marilène Gaudet、Doris Pupowicz、Maurizio Maio、Pierre-André Pittet、Lucia Golzio、Claudio Giachetti、Cynthia Rocha、Gérald Bernardinelli、Yaroslav Filinchuk、Alexander Scheer、Matthias K. Schwarz、André Chollet

  DOI：10.1021/jm701383e

  日期：2008.4.1

  A novel chemical class of potent chemoattractant receptor-homologous expressed on Th2 lymphocytes (CRTH2 or DP2) antagonists is reported. An initial and moderately potent spiro-indolinone compound (5) was found during a high-throughput screening campaign. Structure - activity relationship (SAR) investigation around the carboxylic acid group revealed that changes in this part of the molecule could lead to a reversal of functional activity, yielding weakly potent agonists. SAR investigation of the succinimide functional group led to the discovery of several single-digit nanomolar antagonists. The potency of these compounds was confirmed in a human eosinophil chemotaxis assay. Moreover, compounds (R)-58 and (R)-71 were shown to possess pharmacokinetic properties suitable for development as an orally bioavailable drug.
• TRICYCLIC SPIRO DERIVATIVES AS CRTH2 MODULATORS
  申请人：Merck Serono SA

  公开号：EP1891075B1

  公开（公告）日：2011-10-19
• US8236963B2
  申请人：——

  公开号：US8236963B2

  公开（公告）日：2012-08-07